Plant disease control composition and its use

ABSTRACT

A plant disease control composition comprising a carboxamide compound represented by following formula (I), wherein R 1  represents a hydrogen atom or a methyl group, and R 2  represents a methyl group, a difluoromethyl group or a trifluoromethyl group, and fludioxonil is provided by this invention, and this composition has an excellent effect for controlling plant disease.

TECHNICAL FIELD

The present invention relates to a plant disease control composition andits use.

BACKGROUND ART

Many compounds have been developed for controlling plant diseases andactually used (see, for example, PTL 1 and 2).

CITATION LIST Patent Literature

[PTL 1]: WO86/02641

[PTL 2]: WO92/12970

SUMMARY OF INVENTION Technical Problem

An object of the present invention is to provide a composition having anexcellent effect for controlling plant disease.

Solution to Problem

The inventor of the present invention studied for seeking a compositionhaving an excellent effect for controlling plant disease and found thata composition comprising a carboxamide compound represented by followingformula (I) and fludioxonil has an excellent effect for plant diseasesand then completed the present invention.

The present invention provides the following [1] to [5].

[1] A plant disease control composition comprising a carboxamidecompound represented by formula (I):

wherein

R¹ represents a hydrogen atom or a methyl group, and

R² represents a methyl group, a difluoromethyl group or atrifluoromethyl group, and fludioxonil.

[2] The plant disease control composition according to above [1],wherein the weight ratio of the carboxamide compound to fludioxonil isfrom 0.1/1 to 10/1 of the carboxamide compound/fludioxonil.

[3] A method of controlling plant disease which comprises a step oftreating a plant or the soil where a plant grows with an effectiveamount of a carboxamide compound represented by formula (I):

wherein

R¹ represents a hydrogen atom or a methyl group, and

R² represents a methyl group, a difluoromethyl group or atrifluoromethyl group, and fludioxonil.

[4] The method of controlling plant disease according to above [3],wherein the weight ratio of the carboxamide compound to fludioxonil isfrom 0.1/1 to 10/1 of the carboxamide compound/fludioxonil.

[5] The method of controlling plant disease according to above [3] or[4], wherein the plant or the soil where a plant grows is soybean or thesoil where soybean grows, respectively.

Advantageous Effect of Invention

According to the present invention, various plant diseases can becontrolled.

DESCRIPTION OF EMBODIMENTS

The plant disease control composition of the present invention(hereinafter referred to as “composition”) comprises a carboxamidecompound represented by formula (I):

wherein

R¹ and R² represent the same meanings as defined in the above(hereinafter referred to as “carboxamide compound”) and fludioxonil.

The “carboxamide compound” are those as described in, for example,WO86/02641 or WO92/12970 and can be prepared by the method describedtherein.

Particular examples of the “carboxamide compounds” are as follows:

-   carboxamide compound represented by formula (1):

(hereinafter referred to as “carboxamide compound (1)”);

-   carboxamide compound represented by formula (2):

(hereinafter referred to as “carboxamide compound (2)”);

-   carboxamide compound represented by formula (3):

(hereinafter referred to as “carboxamide compound (3)”):

-   carboxamide compound represented by formula (4):

(hereinafter referred to as “carboxamide compound (4)”);

-   carboxamide compound represented by formula (5):

(hereinafter referred to as “carboxamide compound (5)”).

Fludioxonil is a known compound and described in, for example, “THEPESTICIDE MANUAL—14^(th) EDITION (published by BCPC) ISBN 1901396142.This compound can be obtained from the products containing said compoundin the market or can be synthesized by publicly known methods.

The weight ratio of the “carboxamide compound” to fludioxonil in the“composition” is usually from 0.01/1 to 500/1, and preferably from 0.1/1to 10/1 of “carboxamide compound”/fludioxonil.

Although the “composition” may be a mixture itself of a “carboxamidecompound” and fludioxonil, the “composition” is usually prepared bymixing a “carboxamide compound”, fludioxonil and an inert carrier, andif necessary, by adding a surfactant and/or another auxiliary forformulation and by formulating the mixture into oil formulation,emulsifiable concentrate, flowable formulation, wettable powder, waterdispersible granules, powders granules, or the like. The formulation,which is used alone or by adding another inert component, can be used asa plant disease control agent. The total content of a “carboxamidecompound” and fludioxonil in a “composition” is usually from 0.1% to 99%by weight, preferably from 0.2% to 90% by weight, and more preferablyfrom 1% to 80% by weight.

Examples of the solid carriers used for the formulation include finepowder or granules of, for example, mineral materials such as kaolinclay, attapulgite, bentonite, montmorillonite, acid clay, pyrophillite,talc, diatomaceous earth and calcite; natural organic materials such ascorncob powder and walnut powder; synthesized organic materials such asurea; salts such as potassium carbonate and ammonium sulfate; syntheticinorganic materials such as synthesized hydrous silicon oxide.

Examples of the liquid carriers include aromatic hydrocarbons such asxylene, alkylbenzene and methylnaphthalene; alcohols such as 2-propanol,ethylene glycol, propylene glycol and ethylene glycol mono-ethyl ether;ketones such as acetone, cyclohexanone and isophorone; vegetable oilssuch as soybean oil and cotton seed oil; petrolic aliphatichydrocarbons; esters; dimethylsulfoxide; acetonitrile; and water.

Examples of the surfactants include anionic surfactants such as alkylsulfate ester salts, alkylarylsulfonate salts, dialkylsulfosuccinatesalts, polyoxyethylene alkylaryl ether phosphoric acid ester salts,lignin sulfonate and naphthalene sulfonate formaldehyde polycondensedproducts; non-ionic surfactants such as polyoxyethylene alkyl arylethers, polyoxyethylene alkyl polyoxypropylene block copolymers andsorbitan fatty acid esters; and cationic surfactants such as alkyltrimethyl ammonium salts.

Examples of the other auxiliaries for formulation include water-solublepolymers such as polyvinyl alcohol and polyvinylpyrrolidone;polysaccharides such as gum arabic, alginic acid and its salt, CMC(carboxymethylcellulose) and xanthan gum; inorganic materials such asaluminum magnesium silicate, alumina sol; preservatives; coloringagents; and stabilizers such as PAP (acidic isopropyl phosphate), BHT.

The “composition” can be also prepared by formulating a “carboxamidecompound” and fludioxonil according to the method as described in theabove, and then making the formulation or their diluents.

The “composition” can be used for protecting a plant from a plantdisease.

Examples of plant diseases which can be controlled by the “composition”include the followings.

Rice diseases: Magnaporthe grisea, Cochliobolus miyabeanus, Rhizoctoniasolani, Gibberella fujikuroi;

Wheat diseases: Erysiphe graminis, Fusarium graminearum, F. avenaceum,F. culmorum, Microdochium nivale, Puccinia striiformis, P. graminis, P.recondita Micronectriella nivale, Typhula sp., Ustilago tritici,Tilletia caries, Pseudocercosporella herpotrichoides, Mycosphaerellagraminicola, Stagonospora nodorum, Pyrenophora tritici-repentis;

Barley diseases: Erysiphe graminis, Fusarium graminearum, F. avenaceum,F. culmorum, Microdochium nivale, Puccinia striiformis, P. graminis, P.hordei, Ustilago nuda, Rhynchosporium secalis, Pyrenophora teres,Cochliobolus sativus, Pyrenophora graminea, Rhizoctonia solani;

Maize diseases: Ustilago maydis, Cochliobolus heterostrophus,Gloeocercospora sorghi, Puccinia polysora, Cercospora zeae-maydis,Rhizoctonia solani;

Citrus diseases: Diaporthe citri, Elsinoe fawcetti, Penicilliumdigitatum, P. italicum, Phytophthora parasitica, Phytophthoracitrophthora;

Apple diseases: Monilinia mali, Valsa ceratosperma, Podosphaeraleucotricha, Alternaria alternate apple pathotype, Venturia inaequalis,Colletotrichum acutatum, Phytophtora cactorum;

Pear diseases: Venturia nashicola, V. pirina, Alternaria alternataJapanese pear pathotype, Gymnosporangium haraeanum, Phytophtoracactorum;

Peach diseases: Monilinia fructicola, Cladosporium carpophilum,Phomopsis sp.;

Grape diseases: Elsinoe ampelina, Glomerella cingulata, Uninula necator,Phakopsora ampelopsidis, Guignardia bidwellii, Plasmopara viticola;

Persimmon diseases: Gloesporium kaki, Cercospora kaki, Mycosphaerelanawae;

Gourd diseases: Colletotrichum lagenarium, Sphaerotheca fuliginea,Mycosphaerella melonis, Fusarium oxysporum, Pseudoperonospora cubensis,Phytophthora sp., Pythium sp.;

Tomato diseases: Alternaria solani, Cladosporium fulvum, Phytophthorainfestans;

Eggplant diseases: Phomopsis vexans, Erysiphe cichoracearum;

Brassicaceous vegetable diseases: Alternaria japonica, Cercosporellabrassicae, Plasmodiophora brassicae, Peronospora parasitica;

Welsh onion diseases: Puccinia allii, Peronospora destructor;

Soybean diseases: Cercospora kikuchii, Elsinoe glycines, Diaporthephaseolorum var. sojae, Septoria glycines, Cercospora sojina, Phakopsorapachyrhizi, Phytophthora sojae, Rhizoctonia solani, Corynesporacasiicola, Sclerotinia sclerotiorum;

Kidney bean diseases: Colletrichum lindemthianum;

Peanut diseases: Cercospora personata, Cercospora arachidicola,Sclerotium rolfsii;

Pea diseases: Erysiphe pisi;

Potato diseases: Alternaria solani, Phytophthora infestans, Phytophthoraerythroseptica, Spongospora subterranean, f. sp. Subterranean;

Strawberry diseases: Sphaerotheca humuli, Glomerella cingulata;

Tea diseases: Exobasidium reticulatum, Elsinoe leucospila,Pestalotiopsis sp., Colletotrichum theae-sinensis;

Tobacco diseases: Alternaria longipes, Erysiphe cichoracearum,Colletotrichum tabacum, Peronospora tabacina, Phytophthora nicotianae;

Rapeseed diseases: Sclerotinia sclerotiorum, Rhizoctonia solani;

Cotton diseases: Rhizoctonia solani;

Beet diseases: Cercospora beticola, Thanatephorus cucumeris,Thanatephorus cucumeris, Aphanomyces cochlioides;

Rose diseases: Diplocarpon rosae, Sphaerotheca pannosa, Peronosporaspars;

Diseases of chrysanthemum andasteraceae: Bremia lactuca, Septoriachrysanthemiindici, Puccinia horiana;

Diseases of various plants: Pythium aphanidermatum, Pythium debarianum,Pythium graminicola, Pythium irregulare, Pythium ultimum, Botrytiscinerea, Sclerotinia sclerotiorum;

Radish diseases: Alternaria brassicicola;

Zoysia diseases: Sclerotinia homeocarpa, Rhizoctonia solani;

Banana diseases: Mycosphaerella fijiensis, Mycosphaerella musicola;

Sunflower diseases: Plasmopara halstedii;

Seed diseases or diseases in the initial stage of growth of variousplants caused by Aspergillus spp., Penicillium spp., Fusarium spp.,Gibberella spp., Tricoderma spp., Thielaviopsis spp., Rhizopus spp.,Mucor spp., Corticium spp., Rhoma spp., Rhizoctonia spp., Diplodia spp.,or the like;

Virus diseases of various plants mediated by Polymixa spp., Olpidiumspp. or the like.

Examples of the plants for which the “composition” can be used are asfollows:

Agricultural crops: maize, rice, wheat, barley, rye, oat, sorghum,cotton, soybean, peanut, buckwheat, sugar beet, rapeseed, sunflower,sugar cane, tobacco, and the like;

Vegetables: Solanaceous vegetables (eggplant, tomato, green pepper, hotpepper, potato, etc.), Cucurbitaceous vegetables (cucumber, pumpkin,zucchini, watermelon, melon, squash, etc.); Cruciferous vegetables(radish, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage, brownmustard, broccoli, cauliflower, etc.), Asteraceous vegetables (burdock,garland chrysanthemum, artichoke, lettuce, etc.), Liliaceous vegetables(Welsh onion, onion, garlic, asparagus, etc.), Umbelliferous vegetables(carrot, parsley, celery, parsnip, etc.), Chenopodiaceous vegetables(spinach, chard, etc.), Lamiaceous vegetables (Japanese basil, mint,basil, etc.), strawberry, sweet potato, yam, aroid, and the like;

Flowering plants;

Ornamental foliage plants;

Turf;

Fruit trees: pome fruits (apple, common pear, Japanese pear, Chinesequince, quince, etc.), stone fruits (peach, plum, nectarine, Japaneseplum, cherry, apricot, prune, etc.), citrus (mandarin, orange, lemon,lime, grapefruit, etc.), nuts (chestnut, walnut, hazel nut, almond,pistachio, cashew nut, macadamia nut, etc.), berry fruits (blueberry,cranberry, blackberry, raspberry, etc.), grape, persimmon, olive,loquat, banana, coffee, date, coconut palm, and the like;

Trees other than fruit trees: tea, mulberry, flowering trees, streettrees (ash tree, birch, dogwood, eucalyptus, ginkgo, lilac, maple tree,oak, poplar, cercis, Chinese sweet gum, plane tree, zelkova, Japanesearborvitae, fir tree, Japanese hemlock, needle juniper, pine, spruce,yew), and the like.

The above-described plants may be those having resistance imparted bygenetic engineering technique.

Among the above plants, the “composition” is expected to have excellentcontrolling effect particularly to plant diseases caused in soybean.

Among the above plant diseases, the soybean diseases to which especiallyexcellent effect of the “composition” can be expected are Rhizoctoniasolani, Cercospora kikuchii, Septoria glycines, Corynespora casiicola,Phakopsora pachyrizi, Sclerotinia sclerotiorum, Cercospora sojina, andthe like.

Following compositions exemplify an embodiment of the “composition”:

-   a composition comprising “carboxamide compound (1)” and fludioxonil;-   a composition comprising “carboxamide compound (2)” and fludioxonil;-   a composition comprising “carboxamide compound (3)” and fludioxonil;-   a composition comprising “carboxamide compound (4)” and fludioxonil;-   a composition comprising “carboxamide compound (5)” and fludioxonil;

a composition comprising “carboxamide compound (1)” and fludioxonil inwhich the weight ratio of “carboxamide compound (1)” to fludioxonil is0.1/1 to 10/1;

a composition comprising “carboxamide compound (2)” and fludioxonil inwhich the weight ratio of “carboxamide compound (2)” to fludioxonil is0.1/1 to 10/1;

a composition comprising “carboxamide compound (3)” and fludioxonil inwhich the weight ratio of “carboxamide compound (3)” to fludioxonil is0.1/1 to 10/1;

a composition comprising “carboxamide compound (4)” and fludioxonil inwhich the weight ratio of “carboxamide compound (4)” to fludioxonil is0.1/1 to 10/1;

a composition comprising “carboxamide compound (5)” and fludioxonil inwhich the weight ratio of “carboxamide compound (5)” to fludioxonil is0.1/1 to 10/1.

The method of controlling a plant disease (hereinafter referred to as“controlling method”) can be carried out by treating a plant or the soilwhere a plant grows with an effective amount of a “carboxamide compound”and fludioxonil.

The part of a plant to be treated is stem and leaf of a plant, seed orbulb of a plant, and the bulb means bulb, corm, rootstock, tuber,tuberous root and rhizophore.

In the “controlling method”, the treatment of a plant or the soil wherea plant grows with a “carboxamide compound” and fludioxonil can becarried out separately at the same timing, but the treatment is usuallycarried out by using a “composition” in light of convenience.

In the “controlling method”, the treatment with a “carboxamide compound”and fludioxonil is, for example, stems and leaves application, soilapplication, roots application or seeds application.

Examples of the stems and leaves application include a treatment forsurface of cultivated plant by a stem and leaves spray or a stem andtree spray.

Examples of the root application include a method of dipping a wholeplant or root of a plant into a liquid containing a “carboxamidecompound” and fludioxonil and a method of sticking a solid preparationcomprising a “carboxamide compound”, fludioxonil and a solid carrieronto root of a plant.

Examples of the soil application include a method of spraying a“composition” onto a soil, a method of mixing a “composition” with asoil and a method of irrigating a “composition” into the soil.

Examples of the seed application include a method of treating seeds orbulbs of a plant to be protected from a plant disease with a“composition”. Particularly, the application can be carried out byspraying a suspension of a “composition” to the surface of seeds orbulbs, or by spreading wettable powder, emulsifiable concentrate orflowable formulation itself or a mixture thereof with a small amount ofwater on the seeds or the bulbs, or by dipping the seeds into a solutionof a “composition” for a prescribed time, or by film coating applicationor pellet coating application.

The amount of a “carboxamide compound” and fludioxonil used in the“controlling method” is different depending on the kind of a plant to betreated, the kind of a plant diseases to be controlled and itsfrequency, the kind of a formulation, timing of treatment, method oftreatment, place of treatment, weather condition, and the like.

When a “composition” is applied to stems and/or leaves of a plant or tothe soil where a plant grows, the total amount of a “carboxamidecompound” and fludioxonil is usually from 1 g to 500 g/1000 m²,preferably from 2 g to 200 g/1000 m², and more preferably from 10 g to100 g/1000 m².

When a “composition” is applied to seeds of a plant, the total amount ofa “carboxamide compound” and fludioxonil is usually from 0.001 g to 10g/1 kg of the seeds, and preferably from 0.01 g to 1 g/1 kg of theseeds.

An emulsifiable concentrate, wettable powder or flowable formulation isused usually by diluting the formulation with water and spraying thediluted formulation. In this case, the concentration of a “carboxamidecompound” and fludioxonil in total of the diluted formulation is usuallyfrom 0.0005% to 2% by weight, and preferably from 0.005% to 1% byweight.

A powder formulation, granule formulation, and the like is usually usedwithout dilution.

EXAMPLE

The present invention is further explained in detail with FormulationExamples and Test Examples. However, the present invention is notlimited by the following Examples.

In the following Examples, “part” means “part by weight” unlessotherwise provided.

Formulation Example 1

One of “carboxamide compounds” (1) to (5) (2.5 parts), fludioxonil (1.25parts), polyoxyethylene styryl phenyl ether (14 parts), calciumdodecylbenzene sulfonate (6 parts) and xylene (76.25 parts) arethoroughly mixed to give each of formulations, respectively.

Formulation Example 2

One of “carboxamide compounds” (1) to (5) (2 parts), fludioxonil (8parts), a mixture of white carbon and polyoxyethylene alkyl ethersulfate ammonium salt (ratio by weight 1:1) (35 parts) and water (55parts) are mixed and milled by wet-milling method to give each offormulations, respectively.

Formulation Example 3

One of “carboxamide compounds” (1) to (5) (5 parts), fludioxonil (10parts), sorbitan tri-oleate (1.5 parts) and an aqueous solution (28.5parts) containing polyvinyl alcohol (2 parts) are mixed and the mixtureis milled by wet-milling method. To the milled mixture is added anaqueous solution (45 parts) containing xanthan gum (0.05 parts) andaluminum magnesium silicate (0.1 part), and further propylene glycol (10parts) is added to the mixture. The resultant mixture is mixed bystirring to give each of formulations, respectively.

Formulation Example 4

One of “carboxamide compounds” (1) to (5) (1 part), fludioxonil (4parts), synthesized hydrous silicon oxide (1 part), calciumligninsulfonate (2 parts), bentonite (30 parts) and kaolin clay (62parts) are thoroughly mixed and milled. Water is added to the mixtureand the mixture is sufficiently kneaded, granulated and then dried togive each of formulations, respectively.

Formulation Example 5

One of “carboxamide compounds” (1) to (5) (12.5 parts), fludioxonil(37.5 parts), calcium ligninsulfonate (3 parts), sodium lauryl sulfate(2 parts) and synthesized hydrous silicon oxide (45 parts) arethoroughly mixed and milled to give each of formulations, respectively.

Formulation Example 6

One of “carboxamide compounds” (1) to (5) (3 parts), fludioxonil (2parts), kaolin clay (85 parts) and talc (10 parts) are thoroughly mixedand milled to give each of formulations, respectively.

Test Examples using each of the “compositions” are shown in thefollowing.

Test Example 1

A cyclohexanone solution (100 microL) containing prescribed amount(weight) of a test compound was applied on seeds of soybean(variety:Natto Shoryu) (10 g) by using a rotary apparatus for seedtreatment (Seed dresser, manufactured by Hans-Ulrich Hege GmbH).

One day after the application, plastic pot was filled with soilcontaminated by Rhizoctonia solani, and the seeds treated with the testcompounds were seeded in the soil and cultivated in a glass-greenhousefor 20 days (hereinafter referred to as “treated plot”).

Thereafter, the presence of disease caused by Rhizoctonia solani in theyoung plants which germinated from each seed was observed and diseaseseverity was calculated according to the following calculation formula(1).

On the other hand, seeds of soybean which were not treated as above werecultivated in the same way as above (hereinafter referred to as“non-treated plot”) and disease severity in “non-treated plot” wascalculated in the same way as above “treated plot”. On the basis of theabove disease severity in “treated plot” and “non-treated plot”,efficacy in “treated plot” was evaluated according to the followingcalculation formula (2).

The results are shown in Table 1 and Table 2.Disease severity(%)=(number of infected young plants/total number ofyoung plants)×100  Calculation formula (1)Efficacy(%)=[1−(disease severity in “treated plot”/disease severity in“non-treated plot”)]×100  Calculation formula (2)

TABLE 1 “carboxamide compound (1)” fludioxonil [g/100 kg of seeds][g/100 kg of seeds] efficacy (%) 2 2 100

TABLE 2 “carboxamide compound (5)” fludioxonil [g/100 kg of seeds][g/100 kg of seeds] efficacy (%) 2 2 100Industrial Applicability

A plant disease control composition comprising a “carboxamide compound”represented by formula (I) and fludioxonil is useful for controllingplant disease.

The invention claimed is:
 1. A plant disease control compositioncomprising a carboxamide compound represented by formula (1):

wherein the weight ratio of the carboxamide compound to fludioxonil isfrom 0.01/1 to 500/1 of the carboxamide compound/fludioxonil.
 2. Theplant disease control composition according to claim 1, wherein theweight ratio of the carboxamide compound to fludioxonil is from 0.1/1 to10/1 of the carboxamide compound/fludioxonil.
 3. A method of controllingplant disease which comprises a step of treating a plant or the soilwhere a plant grows with an effective amount of a carboxamide compoundrepresented by formula (1):

wherein the weight ratio of the carboxamide compound to fludioxonil isfrom 0.01/1 to 500/1 of the carboxamide compound/fludioxonil.
 4. Themethod of controlling plant disease according to claim 3, wherein theweight ratio of the carboxamide compound to fludioxonil is from 0.1/1 to10/1 of the carboxamide compound/fludioxonil.
 5. The method ofcontrolling plant disease according to claim 3 or claim 4, wherein theplant or the soil where a plant grows is soybean or the soil wheresoybean grows, respectively.